Vintage Secretary Porn Videos

The sexy secretary was an easy stereotype to propagate in the classical era since the role of the secretary was predominantly reserved for women who served rich and powerful men who handled many activities in their offices. The secretary position is traditionally a role of submission, and the boss is expected to be inherently assertive and dominant.

A sexual relationship between the boss and secretary was convenient, given their constant interaction. In vintage porn, it's not uncommon for bosses to end up fucking their secretaries since they were young and pretty and continuously submitted to the boss.

This page features vintage secretary porn videos from the 1900s to the '70s. It was already a popular fantasy among men who thought of fucking their secretaries and women who could only wish for a sexual relationship with their boss.

Considering the nature of the relationship was cheating, the sex happened at the office. It was as kinky as you would imagine. Bosses with more than one secretary wielded enough influence to summon them to their office and commandeer a group sex, as illustrated in some of the stag films on this page.

Relish B&W stag films from the Edwardian era until the end of World War II and colored scenes produced during the Golden Age of Porn.